57543-40-5

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-2H-chromene-3-carbaldehyde is used as an intermediate in the synthesis of pharmaceuticals for its potential biological activities. It is particularly valued for its antitumor, anti-inflammatory, and antioxidant properties, which make it a promising candidate in the development of new drugs.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 6-Methoxy-2H-chromene-3-carbaldehyde serves as a key intermediate, contributing to the creation of various organic compounds that may have specialized applications across different industries.
Used in Material Science:
6-Methoxy-2H-chromene-3-carbaldehyde is utilized in the development of new materials such as fluorescent dyes and organic electronic devices, thanks to its unique chemical structure and properties, which offer potential for these advanced applications.
Used in Research and Development:
6-METHOXY-2H-CHROMENE-3-CARBALDEHYDE is also used in research and development settings to explore its potential biological activities further and to investigate its role in the synthesis of other beneficial chemical entities.

InChI:InChI=1/C11H10O3/c1-13-10-2-3-11-9(5-10)4-8(6-12)7-14-11/h2-6H,7H2,1H3

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 107-02-8 acrolein 
• 57543-71-2 6-methoxy-2H-chromene-3-carbonitrile 

Downstream Products

• 1407153-06-3 (E)-3-(6-methoxy-2H-chromen-3-yl)-1-(2-methoxyphenyl)prop-2-en-1-one 
• 1407153-04-1 (E)-3-(6-methoxy-2H-chromen-3-yl)-1-(3,5-dimethoxyphenyl)prop-2-en-1-one 
• 1407153-03-0 (E)-3-(6-methoxy-2H-chromen-3-yl)-1-(4-methoxyphenyl)prop-2-en-1-one 
• 1229681-49-5 (E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2H-chromen-3-yl)prop-2-en-1-one 
• 1229681-43-9 (E)-1-(3-chlorophenyl)-3-(6-methoxy-2H-chromen-3-yl)prop-2-en-1-one 
• 1229681-38-2 (E)-3-(6-methoxy-2H-chromen-3-yl)-1-phenylprop-2-en-1-one 
• 1229681-46-2 (E)-1-(4-chlorophenyl)-3-(6-methoxy-2H-chromen-3-yl)prop-2-en-1-one 
• 1229681-40-6 (E)-1-(2-chlorophenyl)-3-(6-methoxy-2H-chromen-3-yl)prop-2-en-1-one 

Relevant academic research and scientific papers

Polyphenols bearing cinnamaldehyde scaffold showing cell growth inhibitory effects on the cisplatin-resistant A2780/Cis ovarian cancer cells

Ovarian carcinoma remains the most lethal among gynecological cancers. Chemoresistance is a clinical problem that severely limits treatment success. To identify potent anticancer agents against the cisplatin-resistant human ovarian cancer cell line A2780/Cis, 26 polyphenols bearing a cinnamaldehyde scaffold were synthesized. Structural differences in their inhibitory effect on clonogenicity of A2780/Cis cells were elucidated using comparative molecular field analysis and comparative molecular similarity indices analysis. Structural conditions required for increased inhibitory activity can be derived based on the analysis of their contour maps. The two most active compounds (16 and 19) were selected and further characterized their biological activities. We found that compounds 16 and 19 trigger cell cycle arrest at the G2/M phase and apoptotic cell death in cisplatin-resistant A2780/Cis human ovarian cancer cells. The molecular mechanism of compound 16 was elucidated using in vitro aurora A kinase assay, and the binding mode between the compound 16 and aurora A kinase was interpreted using in silico docking experiments. The findings obtained here may help us develop novel plant-derived polyphenols used for potent chemotherapeutic agents. In conclusion, compounds 16 and 19 could be used as promising lead compounds for the development of novel anticancer therapies in the treatment of cisplatin-resistant ovarian cancers.

Cytotoxic activity evaluation and QSAR study of chromene-based chalcones

Chalcone and chromene motifs are synthetic or naturally occurring scaffolds with significant cytotoxic profile. Two types of novel regioisomeric chromene-chalcone hybrids, namely 1-(6-chloro or 6-methoxy-2H-chromen-3-yl)-3- phenylprop-2-en-1-one (Type A) and 3-(6-chloro or 6-methoxy-2H-chromen-3-yl)-1- phenylprop-2-en-1-one (Type B), both with different substituents on the phenyl ring attached to propenone linkage, have been evaluated for their cytotoxic activity against breast cancer cell lines (MCF-7 and MDA-MB-231). The results indicate that type A of chromene-chalcones demonstrated better cytotoxic profile than type B especially in MDA-MB-231 cell line. In addition, the growth inhibitory activity of most of the target compounds is higher than Etoposide as a reference drug. QSAR analysis of these novel compounds demonstrated that topological and geometrical parameters are among the important descriptors that influence the cytotoxic activity profile of compounds.

Design, one-pot synthesis, molecular docking study, and antibacterial evaluation of novel 2H-chromene based imidazo[1,2-a]pyridine derivatives as potent peptide deformylase inhibitors

An efficient, environmentally friendly, one-pot three-component synthesis of a series of 2H-chromene-based imidazo[1,2-a]pyridines had been designed and were synthesized. This protocol was developed by the reaction of substituted 2H-chromene aldehydes and

Benzopyran compounds and preparation method thereof as well as pharmaceutical composition and use of benzopyran compounds

The invention discloses benzopyran compounds as shown in a formula I, a preparation method of the benzopyran compounds, a composition containing the compounds, and use of the compounds in preparation of a farnesoid X receptor antagonist, a liver protection agent and medicines for preventing and treating hyperlipidemia and diabetes mellitus type II.

Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice.

A NOVEL FLAVONOID AND USE OF THE SAME

The present invention relates to a novel flavonoid and a use thereof.

A novel chalcone derivative and composition for anticancer comprising the same

The present invention relates to a novel chalcone derivative and an anticancer composition including the chalcone derivative. In the present invention, provided are an anticancer drug for treating ovarian cancer cells and another anticancer drug for treating ovarian cancer cells having resistance to cisplatin. For this, in the present invention, provided is a compound denoted by chemical formula 1 in which R^1 is H or OCH_3, R^2 is OCH_3 or H, R^3 is OCH_3, R^4 is H, R^5 is OCH_3, R^6 is H and R^7 is OCH_3.

Copper-catalyzed enantioselective henry reaction of enals and subsequent iodocyclization: Stereoselective construction of chiral azatricyclic frameworks

In the frame: A cascade sequence combining an asymmetric Henry reaction and a stereoselective intramolecular iodocyclization provides direct access to an enantioenriched tricyclic hexahydrochromeno[4,3-b]pyrrole framework (see scheme). The Henry reaction is catalyzed by copper in the presence of L1. Copyright

1H and 13C NMR spectral assignments of novel chromenylchalcones

Several types of chalcones containing 2H-chromen group were synthesized. Claisen-Schmidt condensation of 2H-chromen-3-carbaldehydes (I) with methoxy substituted acetophenones afforded (E)-3-(2H-chromen-3-yl)-1-(methoxyphenyl) prop-2-en-1-ones (chromenylchalcones, 1-7). Other types of chromenylchalcone, (E)-1-(6-methoxy-2H-chromen-3-yl)-3-(methoxyphenyl)prop-2-en-1-ones (8-13) were also obtained between reaction of methoxy substituted benzaldehydes and 1-(6-methoxy-2H-chromen-3-yl)ethanone (II). Dichromenylchalcones (14-16) were also synthesized through the same reaction between aldehydes (I) and ketone (II). Their complete 1H-NMR and 13C-NMR assignments are reported here and more polysubstituted chromenylchalcones synthesized or isolated from the natural sources in the future can be identified on the basis of the NMR data reported here. Copyright

Efficient one-pot synthesis of ethyl [2-(2H-Chromene-3yl)-4-oxo-L,3- thiazolidin-3-yl]acetates

Ethyl [2-(2H-chromene-3yl)-4-oxo-1,3-thiazolidin-3yl]acetates (6a-e) were synthesized in a single pot by the reaction of 2H-3-chromenecarbaldehydes (3a-e), glycine ethyl ester hydrochloride (4), and mercaptoacetic acid (5) in diisopropylethylamine/benzene under refluxing conditions in a Dean-Stark trap.